Production of color discharge effects with gallocyanine dyestuffs



35- or alkyl, R, the groups OH, NH NH a Patented Apr. 5, 1932 3 UNITED s ATas FATE-NT OFFICE ERNST HUG HEINRICH WEBDENBERG, NEU-ALLSCH'WIL, um BASED, awnnssrenons no mm mm: swrrznnmm) A DURAHD d; HUG ENIN'. B. A), O! BASIL,

IBODUGTION OF COLOR DISCHARGE EFFECTS GALLOGYAII'INE numerous NeDrawlng'; Application filed April 22,

production of color discharge tints can be obtained by selecting, for the usual illuminating discharge process, such gallocyanine dyestufis or derivatives there -of which are derived from a meta-substi 2o tuted alkyl-aniline, and using these in the usual color discharge process with aid of hydrosulphite.

Gallocyanine dyestuffs of this kind may I c be represented by the following general formula:

R on

X B N o o 36 hydrogen -aryl,

O-alkyl, and X a substituent, such as for instance CH a halogen, NH a substituted NI-I or others. Obviously it is also possible to employ, gallocyanine dyestufi's being furthe'r substituted in their oxazine-nucleus,

provided that these bodies still contain the substituent X. This latter originates from a meta-substituted alkyl-aniline which 7 is used for the synthesis of this dyestufi type.

The new process is explained by the following examples:

wherein R represents an alkyl, R

Earample I W p The following printing color is prepared:

g to the principle of reduc- 1229, Serial Io. amass, and in Germany my 2, 1m.

20 grams of the gallo mine d estufl roduc b anllldatlon and sul ihouatlon ot the ocy nlnb obtained from nltrosodleth Lmeta-to nldlne and g llfi$gda corresponding progably to the following (CIHI)IN 0 1K): 0 H1 ONE:

1000 grams.

This color is then printed on cotton which has been dyed with diamine red and the printed material is aged or steamed for 5 mlnutes in the rapid ager or steamer, hungout and washed.

There are thus obtained bright or vividv greenish-blue discharge effects on a diamine red ground.

The corres ending dyestufi which is derived from 'ethylanihne (instead of diethyl-meta-toluidine) yields, under like conditions, only muddy, worthless tints.

E'wwmple II- For the dyestufi used in the print-ing paste described in" Example I there is substituted another which is obtained by converting the. gallocyanine dyestufi from nitroso-dimethylmeta-chloranilme and gallamide into its anilido-compound and by sulphonating the latter dyestufi' which probably corresponds to the following formula:

(501E): NH I m U The color aste is printed on cotton which has previous y been dyed with diamine red, and the material is steamed for 5 minutes in the rapid ager or steamer, hung out'and washed. I The discharge efl'ects thus obtained are dine and gallamide and whic vivid blue of more reddish tint than those obtained according to the procedure of Example l'.

Discharge efiects, however, which are obtained with the corresponding dyestufi derived from dimethylaniline (instead of dimeth l-metwohioraniline) are in contrast mud y and useless.

Example III In this example there is used the gallocyanine dyestufi which is produced by anilidation and sulphonation of the dyestufi obtained from nitrosornonoethyl-meta-toluirohably corresponds to the following I\ N A ee/ fi i so a W .JL

H5 JONES The printing paste has the same composition as that given in Example I. It is printed on a diamine red ground as described in EX- ample I and the material is steamed in like manner. I

The discharge effects are vivid blue, considerably more reddish than those obtained according to Example I or Example 11.

With the corresponding dyestufi' which, instead of from nitroso-monoethyl-metatoluidine, is obtained from nitroso-monoethyl-ortho-toluidine, (the difference consisting merely in the position of the methylgroup) there are 0 tained by following a like procedure tints which are only mud and useless.

' Example IV The following printing paste is prepared:

20 grams of the leuco compound of the gallocyanine dyestnfl produced by splitting 012 the carbox 1 group in the gailocyanine obtained 1:011 nitroso-dimethylmeta-toiuidine and gallic acid, and which probably corresponds to the following formula:

600 grams of neutral starch tragacanth thickening are dissolved in 220 grams of hot water. [like solution is cooled down and there are added grams of hydrosuiphite NF cone. powder and 60 grams 0! a solution ot chromium acetate of 20 B6.

1000 grams.

With respect to the diamine red groundcolors mentioned in the examples, it is question of dyeings obtained with dyestufis referred in the Color Index under Nos. 448,449, 451,452. All these dyestufis can be discharged with reducing agents, i. e. can be destroyed. r

This printing paste is printed on a diamine 'terial to further methylracetyl-meta-phenylencdiamine and I on the other hand from allic acid, gallamide or an ester of gallic aci What we claim is 1. A process for obtaining vivid color dis- :harge efiects according to the principle of reduction, consisting in employing for a discharge printing paste a dyestufi of the gallocyanine series which is derived from 9. metasubstituted alkylaniline, in conjunction with a reducing agent and with the otheringredients as used for the said purpose, in rinting the paste thus obtained upon a ground dyeing capable of being destroyed by reducing agents and in subjecting the material to further treatment for producing illuminating discharge effects.

2. A process for obtaining vivid color discharge efiects according to the principle of reduction, consisting in employing for a discharge printing paste a dyestufi of the gallocyanine series, derived from a meta-substituted alkylaniline and being further substituted in its oxazine-nucleus, in conjunction with a reducing agent and with the other ingredients as used for the said purpose, in printing the paste thus obtained upon a ground dyeing capable of being destroyed by reducing agents and in sub'ecting the material to further treatment or producing i1- luminating discharge effects.

3. A process for obtaining vivid color discharge efiects according to the principle of reduction, consisting in employing for a discharge printing aste a dyestufi of the gallocyanine series erived from a meta-substituted alkylaniline and substituted in its oxazine-nucleus by a sulpho aryl-amino group, in conjunction with a reducin agent and with the other ingredients as use for the said purpose, in rinting the paste thus obtained upon a groun dyeing capable of being destroyed by reducing agents and in subjectm the matreatment for producing illuminating discharge effects.

4. A processfor obtaining vivid color dischar e efiects according to the principle of reduction, consisting in employing for a discharge printing paste a d estufi of the gallocyamne series, derived rom a meta-substituted alkylaniline and substituted in its oxazine-nucleus by a sul ho anilido group, in conjunction w th a re ucing agent and with the other ingredients as used for the said purpose, in printing the paste thus obtained upon a ground dyeing capable of being destroyed by reducing agents and in subjecting the material to further treatment for producing illuminating discharge eifects. 1 5. A process for obtaining vivid color discharge effects according to the principle-of reduction, consisting in employing for a discharge printing paste a dyestufi' of the gallocyanine series derived from a dialkyl-metatoluidine and substituted in its oxazine-nucleus by a sulpho anilido group, in conjunc t1on with a reducing agent and with the other ingredients as used for the said purpose, in

printing the paste thus obtained upon a ground dyeing capable of being destroyed by reducing agents and in sub acting the material to further treatment or producing illuminating discharge effects,

6. A process for obtaining vivid color dis charge efi'ects according to the principle of reduction, consisting in employing for a discharge printing paste a dyestufi of the gallocyanine series derived from diethyl-metatoluidine and gallic acid and substituted in its oxazine nucleus by a sulpho anilido group, in conjunction with a reducin agent and with the other ingredients as used or the said urpose, in printing the paste thus obtained upon a ound dyeing capable of being destroyed by reducing agents and in subject ing the material to further treatment for producing illuminating discharge effects. 7. A process for obtaining vivid color discharge efi'ects according to the principle of 40 reduction, consisting in employin for a discharge printing paste a dyestufi o the gallocyanine series which is derived from a metasubstituted alkylaniline, in conjunctionwith hydrosulphite NF and with the other ingredients as used for the said purpose, in printing the paste thus obtained upon a ground dyeing capable of being destroyed by reducing agents and in subjecting the material to further treatment for producing illuminating discharge efiects.

In witness whereof we have hereunto signed our names this 11th da of April, 1929.

ERNST HU HEINRICH ,WERDENBERG. 

